Acetic Acid → HCID 53760472, compound

HRID 843167Notes

Reaction equation

HRID 843167 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][CH2:18][CH2:19][NH2:20])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].[C:21]([C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)(=O)[CH3:22].C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C1COCC1.C(OCC)(=O)C>[NH3:20].[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][CH2:18][CH2:19][NH:20][CH:21]([C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)[CH3:22])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 95893-AcetylpyridineHCID 510558HCID 510558, compoundHCID 5049666Sodium triacetoxyborohydride

Product 2

HCID 222AmmoniaYield 25%HCID 53760472HCID 53760472, compoundYield 32.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-(3-Amino-propoxy)-3-methyl-benzofuran-2-carboxylic acid ethyl ester (40 mg), 3-acetylpyridine (19 mg) and acetic acid (100 μl) were dissolved in THF (5 ml). The solution was stirred at room temperature for one hour. To the solution was added NaB(OAc)3H (100 mg) and the resulting suspension was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate and washed with saturated sodium hydrogencarbonate solution and water. The organic solvent was dried over anhydrous sodium sulfate and evaporated to dryness. The residue was purified by preparative thin layer chromatography (using dichloromethane:MeOH:ammonia solution (25-28%)=10:1:0.2 as a developing solvent) to give 3-methyl-4-[3-(1-pyridin-3-yl-ethylamino)-propoxy]-benzofuran-2-carboxylic acid ethyl ester (9 mg) as a colorless oil. ESI-MS: m/z 383 (MH+); 1H-NMR (CDCl3): δ 1.40 (3H, d, J=6.5 Hz), 1.44 (3H, t, J=7 Hz), 2.03 (2H, m), 2.58 (3H, s), 2.66 (1H, dt, J1=12 Hz, J2=7 Hz), 2.80 (1H, dt, J1=12 Hz, J2=7 Hz), 3.87 (1H, q, J=6.5 Hz), 4.12 (2H, t, J=6 Hz), 4.43 (2H, q, J=7 Hz),6.59 (1H, d, J=8 Hz), 7.11 (1H, d, J=8 Hz), 7.17 (1H, dd, J1=8 Hz, J2=5 Hz), 7.29 (1H, t, J=8 Hz), 7.68 (1H, br d, J=8 Hz), 8.46 (1H, dd, J1=5 Hz, J2=2 Hz), 8.55 (1H, d, J=2 Hz).

Workup

  1. stirringthe resulting suspension was stirred overnight at room temperature
  2. washwashed with saturated sodium hydrogencarbonate solution and water
  3. dry with materialThe organic solvent was dried over anhydrous sodium sulfate
  4. customevaporated to dryness
  5. customThe residue was purified by preparative thin layer chromatography (

Sources & evidence

ORD record
ord-af4b53fa22d245e28c3c25b52d46030e
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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